Sodium Hydroxide → Chlorazifop

HRID 249199Notes

Reaction equation

HRID 249199 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[C:5]([O:11][C:12]2[CH:25]=[CH:24][C:15]([O:16][CH:17]([CH3:23])[C:18]([O:20]CC)=[O:19])=[CH:14][CH:13]=2)=[N:6][CH:7]=[C:8]([Cl:10])[CH:9]=1>O1CCCC1>[Cl:3][C:4]1[C:5]([O:11][C:12]2[CH:13]=[CH:14][C:15]([O:16][CH:17]([CH3:23])[C:18]([OH:20])=[O:19])=[CH:24][CH:25]=2)=[N:6][CH:7]=[C:8]([Cl:10])[CH:9]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2829855Propanoic acid, 2-[4-[(3,5-dichloro-2-pyridinyl)oxy]phenoxy]-, ethyl ester

Product 1

HCID 173715ChlorazifopYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
52 °C

Procedure

10% Sodium hydroxide solution (170 mL, 0.424 mol) is added to a solution of ethyl 2-{p-[(3,5-dichloro-2-pyridyl)oxy]phenoxy}propionate (79.09 g, 0.212 mol) in tetrahydrofuran with stirring. The reaction mixture is heated to 52° C., stirred for 3 hours, concentrated in vacuo and diluted with water. The aqueous solution is washed with methylene chloride, acidified with concentrated sulfuric acid and extracted with ethyl acetate. The combined organic extracts are dried and concentrated in vacuo to give the title product as a white solid (48.7 g) which is identified by 1H NMR spectral analysis.

Workup

  1. stirringstirred for 3 hours
  2. concentrationconcentrated in vacuo
  3. additiondiluted with water
  4. washThe aqueous solution is washed with methylene chloride
  5. extractionextracted with ethyl acetate
  6. customThe combined organic extracts are dried
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ccf186c65be463b818d6c1b2de5565f
Source dataset
uspto-grants-1993_05
Patent number
US05213606

Reaction notes

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